Synthesis of New Dialkyl 2,2′-[Carbonylbis(azanediyl)]dibenzoates via Curtius Rearrangement

Hasna Yassine; Jamila Bouali; Asmaa Oumessaoud; El Mahdi Ourhzif; Salha Hamri; Abderrafia Hafid; Mostafa Khouili; Maria Dolors Pujol

doi:10.1055/s-0040-1706643

Synthesis, Table of Contents

Synthesis 2021; 53(11): 1971-1979
DOI: 10.1055/s-0040-1706643

paper

Synthesis of New Dialkyl 2,2′-[Carbonylbis(azanediyl)]dibenzoates via Curtius Rearrangement

Hasna Yassine

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane - Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco

,

Jamila Bouali

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane - Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco

,

Asmaa Oumessaoud

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane - Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco

^bLaboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain

,

El Mahdi Ourhzif

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane - Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco

^cUniversité Clermont-Auvergne, CNRS, SIGMA Clermont, ICCF, 63000 Clermont–Ferrand, France

,

Salha Hamri

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane - Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco

^dLaboratoire de Chimie Organique, Organométallique et Valorisation des Substances Naturelles, Faculté des Sciences Agadir, BP 8106, Cité Dakhla Agadir 80000, Université Ibn Zohr, Maroc

,

Abderrafia Hafid

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane - Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco

,

Mostafa Khouili∗

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane - Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco

,

Maria Dolors Pujol ∗

^bLaboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain

› Author Affiliations

Abstract

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Abstract

The 2-(alkylcarbonyl)benzoic acids obtained by esterification of phthalic anhydride are converted into azide derivatives: alkyl 2-[(azidocarbonyl)amino]benzoates and to ureas: dialkyl 2,2′-[carbonylbis(azanediyl)]dibenzoates. These transformations were carried out using classical Curtius rearrangement conditions in the presence of diphenylphosphoryl azide (DPPA) in a basic medium, followed by hydrolysis. Subsequently, a final condensation reaction of these urea derivatives enabled us to obtain, for the first time, the new alkyl derivatives, alkyl 2-[2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl]benzoates. All the new compounds obtained in satisfactory yields were characterized by ¹H and ¹³C NMR, and by X-ray crystallographic analysis.

Key words

phthalic anhydride - Curtius rearrangement - azide - acyl azide - urea

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